My recollection is that Civilization (1) came on 5 (? 7?) floppy disks for Mac, but only the first disk was needed for the full game in black and white; the additional disks were needed for color and some add-on assets like improving your palace.
"Build a game that stands the test of time as well as Civilization" is a pretty high bar. 1.44 MB is huge.
the requirement is too vague. whats the OS? are common dll (assuming windows) like msvcrt included in the 1.44 MB size or not? .Net runtime also usually installed, will it count too?
A well written, well thought out text based game would crush this competition
Until relatively recently in computing history, games (and all other programs) were small. Hell, Pokemon Gold fits un a floppy trivially compressed, together with a working GBC emulator. I can trivially fit rePalm unto a floppy and leave enough space for a great PalmOS RTS - "Warfare Inc"
While I can appreciate the general concept of designing withing limitations, 1.44MB just isn't quite the limit it's being presented as. Look at Pico-8 games, for example. With the full Pico-8 runtime environment bundled in, typical games still clock in well under 1MB for Windows builds, and even smaller for Linux (macOS builds bloat up to 3+ MB, unfortunately). That's an entire virtual console + a full game, and still half a meg to spare on a floppy.
POOM, the DOOM clone, is a "multi-cart" on the Pico-8 and still only comes in at 1.2MB on Windows. I guess what I'm getting at is, if someone wants a fast-track to meeting the challenge of 1.44MB, make a Pico-8 game.